Antonio Bertone can’t forget that fateful day he met the quiet young girl who changed everything.
It was the fall of 1997, one evening in Los Angeles, where Bertone, then in his mid-20s, worked as a global director of brand management for the German sportswear company Puma.
At the time, Regency Enterprises held the claim as Puma’s principal shareholder. The mastermind of that unique union of entertainment, footwear and apparel was Regency founder Arnon Milchan, a successful business executive from Israel who became the high-profile film producer behind blockbusters such as Pretty Woman (1990), JFK (1991) and L.A. Confidential (1997). Milchan always thought big picture and had one secretly ambitious plan for Puma, surrounding his off-screen obsession with tennis.
“I got a call from Arnon’s assistant,” Bertone remembered. “She said, ‘Hey, can you come over to the studio tonight around 5 or 6 o’clock? Arnon wants you to join this meeting.’ I was like, ‘OK. Any idea of what the meeting is about?’ She said, ‘I have no idea.’ ”
Around 5:30 p.m., Bertone arrived at Milchan’s office, then located on the lot of Warner Bros. Studios. The meeting had lasted since midday.
“Sitting in the office is Serena Williams,” he recalled. “I don’t think she was even 16 yet.”
Williams, who turns 40 this week, would go on to endorse Puma into her early 20s, wearing custom-designed outfits that made her into a revolutionary of tennis fashion. But her ongoing 18-year partnership with Nike, the brand she’d join in 2003, has overshadowed the oft-forgotten first endorsement deal of her career. It all began, for Williams, with an offer from Puma, negotiated in this meeting.
Next to her in the room sat Richard Williams, who moved his family from Saginaw, Michigan, to Compton, California, in 1983. He taught the game of tennis on the city’s public courts to his daughters, Venus and Serena, who are 15 months apart.
Milchan had met his ultimate match in Richard Williams. The self-proclaimed “James Bond” (who once said that he covertly negotiated arms deals for the Israeli government in the 1960s) took serve against “King Richard,” the hands-on father who leveraged his elder daughter, Venus, an eight-figure endorsement deal with Reebok in 1995. That same year, Williams turned pro at 14, joining her sister on the WTA tour.
“Arnon recognized Serena and Venus’ ability to change the sport of tennis,” Bertone said. “Puma wasn’t in tennis then. But Arnon went from 0 to 100 … like, ‘We’re totally getting back into tennis with Serena.’ ”
Technically, Milchan didn’t have the power to discuss financial terms on Puma’s behalf. And Bertone didn’t have the authority to offer a multiyear contract to an athlete. So they called Puma CEO Jochen Zeitz in Germany. Zeitz woke up in the middle of the night to sign off on the deal. Back in the corner of the LA office, Richard Williams periodically called his wife Oracene on the room’s landline to provide updates. “I was convinced he wasn’t even talking to her,” Bertone noted. “That he was just buying time, drawing things out to see where we’d end up.”
At one point, as detailed in her 2009 autobiography, On The Line, Williams placed her head down on the conference table and dozed off. Negotiations went past midnight, lasting more than 12 hours. The meeting ultimately ended with a multimillion-dollar commitment from Zeitz and Puma, and a verbal agreement from Richard and Serena Williams.
“It was really hard to imagine how her career would evolve,” Bertone said. “But you had to believe, right? It was like, ‘We’re gonna do this.’ At the same time, I kept on going into these obsessive, compulsive loops in my head … like, ‘How the f— are we gonna figure this out?’ ”
Williams, now with 23 Grand Slam singles titles to her legacy, has since been transformed into one of the most admired — and scrutinized — athletes of all time in sport and style. But in the late ’90s, both Puma and a young Williams had much to prove.
“I wanted a sponsor. I wanted someone to believe in me,” wrote Williams in On The Line. “It wasn’t just Puma taking a chance on me. It was me taking a chance on Puma. It cut both ways.”
A week or so after that initial meeting, a large package addressed to Williams arrived at her family’s home in Florida. She opened it and tried on everything inside, gaining validation extending beyond how each outfit appeared in the mirror. It was about more than just the free clothes or even her first endorsement deal.
“It was this moment,” she wrote in On The Line, “going through this giant box of Puma gear that all fit perfectly, where I felt I’d finally arrived as a player.”
By February 1998, approximately five months after negotiations on the Warner Bros. lot, Puma officially announced its partnership with a 16-year-old Serena, then the No. 41-ranked women’s singles player in the world.
“I could have signed with any sports brand, but this was the most promising and felt right for me,” Williams said at the time. (Due to scheduling, Williams declined The Undefeated’s request to be interviewed for this story.)
The unprecedented agreement not only included her promotion of the company’s sportswear products, but also said that she would “participate in various film, music and media projects produced by Regency,” according to The Hollywood Reporter.
Spoiler: Regency never landed Williams on the silver screen (even though the Los Angeles Times reported in March 1999 that she and her sister completed screen tests for an undisclosed film). But Puma certainly delivered in fostering the tennis phenom’s passion for design. Williams made sure she made the most out of the partnership in that regard.
For her first meeting with Alden Sheets, who became president of worldwide apparel at Puma in 1997, Williams came prepared. She gave him a handwritten note and outfit sketches she drew herself while on tour.
“Alden,” wrote Williams, who, at 16, had her own custom-branded letterhead, adorned with her first and last name at the top of each page. “Here are some of the designs that I have thought of. There were many more but this requires many late nights and hard work, especially during a tournament.” On two sheets of paper, Williams outlined her vision for on-court apparel she called the “Petal” and “Mod” series. She traced concepts for jackets, dresses, biker shorts and pants that she filled in with colored pencils and added explanatory notes.
“As I said before,” she continued, “Puma is behind in a lot of ways. And I believe I can help bring the company back to its feet and into the lead once again.”
Remember, Puma didn’t have a presence in tennis when the company signed her. More than a decade had passed since Boris Becker and Martina Navratilova last repped the brand on the court. “We exited tennis in the ’80s, vowing to never get back,” said Bertone, who would become Puma’s chief marketing officer before leaving the company in 2012. Yet Puma returned with Williams. She was an athlete — from her background to the frame of her body and the way she moved — unlike any other the brand had experienced.
“I saw her and Venus play doubles at Wimbledon. These amazing, powerful women of color in sport,” said Amy Denet Deal, a former senior women’s designer for Puma, who is Native American. “Being a woman of color, it was groundbreaking to see that shift.”
Then overseeing a design office in Herzogenaurach, Germany, where the company is headquartered, Deal received the assignment of being Williams’ first lead designer. Puma also paired Williams with Linda Long, a former tennis player-turned-marketing director who operated as a daily brand manager, traveling with her on tour. Deal and Williams first met at a tournament in Indian Wells, California, and bonded over a shared love for apparel in eye-catching colors. Williams gave Deal drawings depicting what she dreamed of wearing on the court.
“I just thought that was the coolest thing ever that this young woman showed up with a bunch of sketches,” said Deal, now the owner and creative director of a design consulting firm and sustainable upcycling brand. “You’re talking about someone who was 17 and had no training in design. She wanted to be the most powerful player. But this effortless sense of style that she’s developed over all these years — that was in her heart.”
Deal designed the yellow dress Williams wore when she won the US Open in September 1999 after upsetting world No. 1 Martina Hingis, 6-3, 7-6, in straight sets. At 17, she became the first African American woman to claim a Grand Slam singles title since Althea Gibson in 1958. She also won the tournament’s women’s doubles title with her sister Venus. Puma celebrated Williams’ first career major singles victory with a $500,000 bonus. And a few weeks later, her tennis coronation gown hit the rack at the first Puma store in the United States, which opened in Santa Monica, California.
“Head-to-toe yellow,” Deal said. “Quite different from what would be expected. It was so beautiful. Back when she first started playing and had all the beads in her hair, she was always matching them with her outfit.”
Her career-long catalog of on-court outfits considered, Williams’ Puma dress from the 1999 US Open is relatively tame. It took some time for her to get comfortable with the brand as she grew into a young woman.
She turned 18. She transitioned from beaded braids to new hairstyles. She announced a joint plan with her sister Venus for offseason enrollment at the Art Institute of Fort Lauderdale, where they would major in fashion. And, most importantly, she started winning. By the end of 1999, she ranked No. 4 in the world in women’s singles.
“Our eye was always on majors,” Sheets said. “Every major, there would be a new series of apparel and a statement outfit. We started conservatively. Then we started to get wild.”
A young designer named Bonnie Dominguez, who specialized in lifestyle clothing, took over as the visionary behind Williams’ apparel after Deal left the company in November 1999. Closer to Williams in age, Dominguez and the tennis star clicked immediately. Williams nicknamed the 5-foot-2 Dominguez “Little Bonnie.”
“Serena was always the muse,” said Dominguez, who designed for Puma from 1998 to 2005. She’s been with New Balance since 2013. “I don’t know if that could’ve happened with any other player — to take that many fashion risks that early in a career. I don’t think the world was ready for it. I don’t think design was ready for it.”
In 2000, classes at the Art Institute started for Williams, who was deemed the “single-most recognizable athlete Puma endorses worldwide” in The Palm Beach Post by the brand’s head of U.S. marketing. She also began addressing her outfits in news conferences, while opening up more about her lifelong love of fashion. Williams quipped, however, that design didn’t come to her as naturally as tennis.
“I like drawing ideas of things to wear and just, like, sketching out things,” she said in 2000. “I’m not the greatest artist, but I’ve got ideas.”
Ahead of the 2000 US Open, Sheets discovered a new type of fabric and a factory in LA that could manipulate it through a unique tie-dyeing process. He challenged Dominguez to use his findings in her debut ensemble for Williams to wear at that season’s final major.
“One of the first outfits that got the most attention was Williams’ purple and black tie-dye coverup,” Sheets said. “She had a pair of compression shorts underneath a bare midriff and bra top. So, at various angles, you were seeing through that garment, because it was mesh. That outfit had the WTA calling me to question what we were doing to tennis, which was a very white, conservative sport.”
The policing of Williams’ style started early in her career. Notably at Wimbledon, tennis’ most revered Grand Slam, where there’s a No. 1 rule: Competitors must be dressed in suitable tennis attire that is almost entirely white. During Williams’ five-year partnership with Puma, certain tournaments began mandating that the brand show Williams’ outfits in advance. Sheets fielded frequent calls from tennis officials, including one that still stands out from the All England Club, where Williams won Wimbledon singles titles in 2002 and 2003.
“I remember I was on a shopping tour, walking the streets of Florence and my cellphone rings,” recalled Sheets. “It was the head of the Wimbledon approval committee saying, ‘Mr. Sheets, we’re very concerned Serena’s outfits will be outside of the ethics of our organization. We’d very much like to see what you’re planning to have her wear. In fact, send the garments to us for our pre-approval before she’s allowed to be on court.’
“I was stunned,” Sheets continued. “The people at Wimbledon were worried we were gonna put Serena out there in a red outfit or something. We wanted to. But we knew we couldn’t get it done. Not there.”
Puma truly flipped the script of traditional tennis attire at the French Open in 2002. The tournament was held during the first two weeks of the FIFA World Cup in South Korea. The marketing team at the brand, which also sponsored Cameroon’s national men’s soccer team, came up with the crazy concept of outfitting Williams in a dress resembling the kit the African nation would wear at the World Cup. Dominguez sketched a sample and pitched it to Williams, who loved the idea. In her opening match at the French Open, she took the court in Cameroon-themed apparel, down to a pair of yellow soccer socks pulled up to her knees.
After Williams won the French Open and at Wimbledon in 2002, Puma needed another head-turning design for the 21-year-old star, who had reached the world No. 1 in women’s singles. She was preparing to compete for her third straight Grand Slam title at the US Open.
“With her pushing so many style boundaries, it was like, ‘What do we do next?’ ” Dominguez remembers thinking. “Does it have to be a skirt? Does it have to be a dress?”
A better question, she asked herself: “How do we make a statement?”
Sketches and design materials were sprawled across her hotel room in Germany as Dominguez prepared for a sales meeting to introduce what she had in store for Williams.
From the television in the background, Dominguez heard speculation that actress Halle Berry was being cast as the lead in the film Catwoman. She turned around and watched the program roll vintage footage of the actress Eartha Kitt, who in 1967 became the first African American woman to star as the comic book character in the TV series Batman.
It was in this moment that Dominguez found inspiration for Williams’ infamous catsuit that she’d debut months later at the 2002 US Open.
“I don’t think anyone else would’ve looked good in that catsuit,” said Dominguez, who immediately got to drawing after “badass Eartha Kitt” reminded her of Williams. For the outfit, she planned to use Lycra, a high-shine spandex brand that looked like faux leather and would tightly hug Williams’ muscular physique. Dominguez complemented the look with a biker-style jacket that she could wear over the catsuit while warming up.
“ ‘Let’s try it,’ ” recalled Dominguez of the customary approval Williams gave to move a design concept into production. By the time Sheets delivered a sample at a memorable 7 a.m. fitting session in her hotel room at the Beverly Hills Four Seasons, Williams had forgotten about the rebellious outfit.
“We hand her the catsuit and she says, ‘This is for me … to wear playing tennis?’ ” Sheets recalled. “She went into the bathroom and came out where there was a full mirror in front of the door. She was just glowing, with this huge grin on her face.”
At the sight of Williams in the catsuit for the first time, Sheets’ split conscience spoke up.
“I remember very specifically having two guys on my shoulders. One on my left and one on my right,” Sheets said. “The one on my left said, ‘You are absolutely crazy if you’re gonna have her walk out at the US Open, upset the USTA, the WTA and have Puma scrutinized. … You can’t allow this.’
“The one on my right said, ‘This is the most incredible thing we’ve ever done. We’re gonna upset all of tennis. We’re gonna upset the entire world. The press is gonna be all over this. And Serena loves it. We’re not turning back at this point.’ ”
Due to delays at a factory in China, the catsuit almost didn’t make it in time for the US Open. At the 11th hour, a Puma representative flew the garment from Hong Kong to New York, where Sheets picked it up at the airport. He handed it off to Long, Williams’ brand manager, who gave it to her and advised she try it on before her opening match at the US Open.
“I had to beg Jim Curley, who was the tournament director then, to allow Serena to wear it. He thought I’d lost my mind but gave the OK,” Long said. “I’m standing in the hallway waiting for Serena to come out to go on to Arthur Ashe Stadium court in the catsuit. She bends over and whispers in my ear, ‘This is the first time I’ve put this catsuit on … hope I don’t lose.’ ”
On Aug. 26, 2002, Williams stepped onto the tennis court and unzipped her jacket to unveil her skintight catsuit. Later that evening, this is how CNN anchor Anderson Cooper opened the program:
“Good evening, everyone. We faced a bitterly divisive issue at our afternoon meeting today. … Now, we could lie and say the fight was whether to invade Iraq or not. … No, today’s tiff was about females and fashion. … We’re talking about tennis supernova Serena Williams and the controversy over the catsuit.”
Despite widespread criticism, Williams went on to win the 2002 US Open, defeating her sister Venus while wearing the outfit that she accented in the final match with a pink headband and armband.
“Man, that outfit turned a lot of heads …,” wrote Williams years later in On The Line. “But what most people don’t realize is it was so comfortable! Of course the catsuit was so hot I would have worn it even if it was the most uncomfortable thing in the world.”
It doesn’t feel like common knowledge that Puma designed the first catsuit Williams wore in her career. Type “Serena catsuit” in Google, and the first images and news stories that surface are those surrounding the Nike one she wore at the French Open in 2018 that the French Tennis Federation barred from returning, saying “one must respect the game.” Nike responded to the ban and comments by releasing an ad with the powerful tagline: “You can take a superhero out of her costume, but you can never take away her superpowers.”
“Serena’s legacy with Puma feels like it all got erased when she went to Nike,” Bertone said.
In December 2003, after winning her first six Grand Slam singles titles while repping Puma, Williams left the company to join Nike on an eight-year endorsement deal reported to be worth up to $55 million with performance incentives. By comparison, Williams earned a reported $13 million from Puma in the first five years of her career. (Dominguez recalled that Williams never had the opportunity to wear the final outfit she designed for her. So Puma outfitted actress Kirsten Dunst in it for the 2004 film Wimbledon.)
“At the time, we went as high as we could go for an athlete, knowing full well that Nike would outbid us,” Bertone said. “People nowadays have no idea about Serena and Puma.”
There’s a memory in particular that Bertone cherishes from Williams’ early days with Puma. In the late ’90s, they crossed paths at the Atlanta Super Show, a sporting goods trade convention.
“I remember seeing her and shaking her hand, like, ‘Holy s—. You’re a superstar now,’ ” Bertone recalled. “She had become a young woman and was much taller than the first time I saw her. She was wearing all her Puma apparel and it was just so nice to be like, ‘This is working!’ ”
She’s since gone from a promising 16-year-old athlete a brand took a chance on to reaching the pinnacle of both tennis and style-bending.
“I consider her a fashion icon,” said Deal, the first Native American designer Williams worked with at Puma. “She’s completely changed the way that women dress for sport.”
In 2019, Williams and Nike teamed up to create an apprenticeship program to promote diversity in design and provide a foundation for a new generation of designers from underrepresented backgrounds. In August, Nike announced the Serena Williams Design Crew’s first collection, set for a fall release, featuring apparel, footwear and accessories and crafted by 10 designers from diverse backgrounds.
Now, it seems, Williams is the one on the receiving end of a young aspiring designer’s sketches.